Over the course of the twentieth century, education was a key site for envisioning opportunities for African Americans, but the very schools they attended sometimes acted as obstacles to black flourishing. Educating Harlem brings together a multidisciplinary group of scholars to provide a broad consideration of the history of schooling in perhaps the nation’s most iconic black community. The volume traces the varied ways that Harlem residents defined and pursued educational justice for their children and community despite consistent neglect and structural oppression. Contributors investigate the individuals, organizations, and initiatives that fostered educational visions, underscoring their breadth, variety, and persistence. Their essays span the century, from the Great Migration and the Harlem Renaissance through the 1970s fiscal crisis and up to the present. They tell the stories of Harlem residents from a wide variety of social positions and life experiences, from young children to expert researchers to neighborhood mothers and ambitious institution builders who imagined a dynamic array of possibilities from modest improvements to radical reshaping of their schools. Representing many disciplinary perspectives, the chapters examine a range of topics including architecture, literature, film, youth and adult organizing, employment, and city politics. Challenging the conventional rise-and-fall narratives found in many urban histories, the book tells a story of persistent struggle in each phase of the twentieth century. Educating Harlem paints a nuanced portrait of education in a storied community and brings much-needed historical context to one of the most embattled educational spaces today.